Vacation Rentals
40 properties available
Welcome to Sol Mate!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementBeautifully updated, fresh, and clean elevated 3 Bed, 2.5 Bath which sleeps up to 8 within easy walking distance to Bean Point beaches & Close to Anna Maria's Beloved Pine Avenue1500 square feetHIGHLIGHTS:-
Sol Mate
Anna Maria
$324.00 - $880.00 / per night
3
bedrooms
2
baths
8
guests
5
(9)
Welcome to Cozy Cabana East!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Renovated Pristine Home w/ Private Pool in Holmes Beach, 6-8 min walk to beachHIGHLIGHTS:- Kitchen, Dining, Living w/ Queen Sleeper Sofa & TV- 1 King Bedroom, En-Suit
Cozy Cabana East
Holmes Beach
$240.00 - $675.00 / per night
2
bedrooms
2
baths
6
guests
5
(5)
Welcome to AcquaLuxe!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.3137 sq. ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom- 1 King Bedroom w/ TV, En-Suite Full Bathroom- 1 King Bedr
AcquaLuxe
Anna Maria
$700.00 - $2,200.00 / per night
4
bedrooms
4
baths
10
guests
5
(6)
Welcome to Sandy Pants!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.2150 sq. ft.HIGHLIGHTS:- Kitchen, Dining, Living w/ TV- 1 King Bedroom - 1 Queen Bedroom - 1 Custom Bunk Room w/ 3 Twin Beds and 2 Double Beds- Sleeper SofaPool Area
Sandy Pants
Holmes Beach
$355.50 - $765.00 / per night
3
bedrooms
2
baths
8
guests
5
(33)
Welcome to Fins Up!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.New Home w/Private Heated Pool & 4 Min Walk to Beach w/Beach Gear!1250 sq. ft.HIGHLIGHTS: - Kitchen, Dining, Living w/ Soaring Ceilings & Queen Sleeper Sofa & TV- 1 Ki
Fins Up
Holmes Beach
$300.00 - $675.00 / per night
2
bedrooms
2
baths
6
guests
5
(9)
Welcome to Family Tides - Unit AOn Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals1200 sq ft.This home is located in a duplex that has two units. This listing is for the second floor Unit A ONLY with 3 bedrooms and 2 bathrooms and access to the property's shared heated pool, rooftop deck and parking. The individu
Family Tides - A
Bradenton Beach
$260.00 - $880.00 / per night
3
bedrooms
2
baths
8
guests
Welcome to Salty Pirate!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.2512 sq. ft.Need more room? Reserve the sister 4 bedroom home next door, Seaswept Mermaid (#1850215), to stay at The Pirate and His Mermaid homes for a total of 8 bedrooms!HIGHLIGHT
Salty Pirate
Anna Maria
$302.40 - $980.00 / per night
4
bedrooms
3
baths
8
guests
5
(6)
Welcome to Shore's Nice!On Anna Maria Island (Anna Maria, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Renovated Pristine Modern Beach Cottage w/ Peek-A-Boo Bay ViewsHIGHLIGHTS:- Kitchen, Dining, Living w/ TV- 1 King Bedroom, En-Suite Full Bathroom- 1 King Bedroom- Full Hall
Shore's Nice
Anna Maria
$265.50 - $612.00 / per night
2
bedrooms
2
baths
4
guests
5
(9)
Welcome to AMI Peppertree Paradise!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.1970 sq. ftHIGHLIGHTS:- Kitchen, Dining Area, Living w/ TV- 1 King Bedroom w/ TV and Ensuite Full Bath & Walk-In Closet- 1 Queen Bedroom w/ TV- 2 Bunk Beds w/Trundle
AMI Peppertree Paradise
Anna Maria
$332.10 - $880.00 / per night
3
bedrooms
2
baths
8
guests
5
(1)
Welcome to Seaswept Mermaid!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals2512 sq. ft.Need more room? Reserve the sister 4 bedroom home next door, Salty Pirate (#1678416), to stay at The Pirate and His Mermaid homes for a total of 8 bedrooms!HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV, Ple
Seaswept Mermaid
Anna Maria
$360.00 - $1,400.00 / per night
4
bedrooms
3
baths
8
guests
5
(7)
Welcome to She's Always Right!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation RentalsThis spacious, bright, and luxurious island home is ready to bring some laughter and memories to you and your group! This home is located just a quick skip to the beach, local restaurants, shops and centrally located on the island!
She's Always Right
Holmes Beach
$380.00 - $1,350.00 / per night
4
bedrooms
4
baths
8
guests
5
(12)
Welcome to Island Girl West!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.A spectacular vacation half-duplex that promises an unparalleled escape on Anna Maria Island.HIGHLIGHTS:- Short Walk to Beach- Kitchen, Dining, Indoor/Outdoor Living
Island Girl West
Holmes Beach
$225.00 - $495.00 / per night
2
bedrooms
2
baths
6
guests
5
(2)
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